HCID 15052973, compound → HCID 431943, compound

Participants

Reaction Steps

2-(3,4-Diaminophenyl)acetic acid can be prepared by acetylation of 2-(4-aminophenylacetonitrile with acetic anhydride in pyridine. The 2-(4-acetamidophenyl)acetonitrile product is nitrated in acetic anhydride to provide 2-(3-nitrile-4-acetamidophenyl)acetonitrile. The nitrile is hydrolyzed with concentrated hydrochloric acid to give 2-(3-nitro-4-aminophenyl)acetic acid after neutralization. The nitro acid is then hydrogenated at 60 psi at room temperature over palladium-on-carbon to yield 2-(3,4-diaminophenyl)acetic acid. The acid can be esterified with C1 -C8 carbinols in the presence of acid catalysts to yield starting materials according to II in which R3 is an ester group. Similarly, the preparation of 2-(3,4-diaminophenyl)propionic acid begins with 2-(4-aminophenyl)propionitrile as described above for the preparation of the diaminophenylacetic acid.

Provenance & Evidence